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Pharmaceuticals
Volume 18
Issue 4
10.3390/ph18040521
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Article

New Cannabinoids and Chlorin-Type Metabolites from the Flowers of Cannabis sativa L.: A Study on Their Neuroblastoma Activity

by
Tuan-Quoc Nguyen
1,
Hyo-Shin Park
1,
Sun-Hyeong Choi
1,
Da-Yun Hong
1,2,
Jae-Yong Cheon
1,
Young-Mi Lee
1,
Chul-Min Kim
3,
Jong-Ki Hong
4,
Seo-Jeong Oh
4,
Man-Soo Cho
5,
Jang-Hoon Kim
6,
Eun-Sol Lee
7,
Jungwon Seo
7 and
Hyun-Ju Jung
1,*
1
Department of Oriental Pharmacy, College of Pharmacy and Wonkwang-Oriental Medicines Reseach Institute, Wonkwang University, Iksan 570-749, Republic of Korea
2
Korean Ministry of Food and Drug Safety, Osongsaengmyeong 2-ro 187, Cheongju 28159, Republic of Korea
3
Department of Horticulture Industry, Wonkwang University, Iksan 54538, Republic of Korea
4
College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea
5
Department of Smart Experience Design, Kookmin University, Seoul 02707, Republic of Korea
6
Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA, Eumseong 27709, Republic of Korea
7
Institute of Pharmaceutical Research and Development, College of Pharmacy, Wonkwang University, Iksan 54538, Republic of Korea
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2025, 18(4), 521; https://doi.org/10.3390/ph18040521
Submission received: 6 March 2025 / Revised: 28 March 2025 / Accepted: 1 April 2025 / Published: 3 April 2025
(This article belongs to the Special Issue Pharmacologically Active Compounds from Plants)
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Abstract

Background/Objectives: Cannabis sativa has been utilized for medical purposes for thousands of years. It continues to be recognized as a plant with an extensive variety of medicinal and nutraceutical uses today. In this study, a chemical investigation of the flowers of C. sativa isolated by using a variety of chromatographic techniques led to the isolation of eleven compounds. These purified compounds were evaluated for antitumor activity against SK-N-SH neuroblastoma cells. Methods: The compounds were isolated by using chromatographic techniques. Their structures were identified by the examination of spectroscopic methods, including 1D (1H, 13C, and DEPT) and 2D (COSY, HSQC, HMBC, and NOESY) nuclear magnetic resonance (NMR) spectra and mass spectrum, together with the comparison to those reported previously in the literature. The evaluation of toxicity on SK-N-SH cells was performed by the MTT method. Results: Eleven compounds were isolated from the flowers of C. sativa, including two new compounds, namely cannabielsoxa (1), 132-hydroxypheophorbide c ethyl ester (2), and six known cannabinoids (6–11), together with the first isolation of chlorin-type compounds: pyropheophorbide A (3), 132-hydroxypheophorbide b ethyl ester (4), and ligulariaphytin A (5) from this plant. The results also demonstrated that cannabinoid compounds had stronger inhibitory effects on neuroblastoma cells than chlorin-type compounds. Conclusions: The evaluation of the biological activities of compounds showed that compounds 4–10 could be considered as the potential compounds for antitumor effects against neuroblastomas. This is also highlighted by using docking analysis. Additionally, the results of this study also suggest that these compounds have the potential to be developed into antineuroblastoma products.
Keywords: Cannabis sativa L.; cannabinoid; chlorin-type compound; SK-N-SH cells Cannabis sativa L.; cannabinoid; chlorin-type compound; SK-N-SH cells

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MDPI and ACS Style

Nguyen, T.-Q.; Park, H.-S.; Choi, S.-H.; Hong, D.-Y.; Cheon, J.-Y.; Lee, Y.-M.; Kim, C.-M.; Hong, J.-K.; Oh, S.-J.; Cho, M.-S.; et al. New Cannabinoids and Chlorin-Type Metabolites from the Flowers of Cannabis sativa L.: A Study on Their Neuroblastoma Activity. Pharmaceuticals 2025, 18, 521. https://doi.org/10.3390/ph18040521

AMA Style

Nguyen T-Q, Park H-S, Choi S-H, Hong D-Y, Cheon J-Y, Lee Y-M, Kim C-M, Hong J-K, Oh S-J, Cho M-S, et al. New Cannabinoids and Chlorin-Type Metabolites from the Flowers of Cannabis sativa L.: A Study on Their Neuroblastoma Activity. Pharmaceuticals. 2025; 18(4):521. https://doi.org/10.3390/ph18040521

Chicago/Turabian Style

Nguyen, Tuan-Quoc, Hyo-Shin Park, Sun-Hyeong Choi, Da-Yun Hong, Jae-Yong Cheon, Young-Mi Lee, Chul-Min Kim, Jong-Ki Hong, Seo-Jeong Oh, Man-Soo Cho, and et al. 2025. "New Cannabinoids and Chlorin-Type Metabolites from the Flowers of Cannabis sativa L.: A Study on Their Neuroblastoma Activity" Pharmaceuticals 18, no. 4: 521. https://doi.org/10.3390/ph18040521

APA Style

Nguyen, T.-Q., Park, H.-S., Choi, S.-H., Hong, D.-Y., Cheon, J.-Y., Lee, Y.-M., Kim, C.-M., Hong, J.-K., Oh, S.-J., Cho, M.-S., Kim, J.-H., Lee, E.-S., Seo, J., & Jung, H.-J. (2025). New Cannabinoids and Chlorin-Type Metabolites from the Flowers of Cannabis sativa L.: A Study on Their Neuroblastoma Activity. Pharmaceuticals, 18(4), 521. https://doi.org/10.3390/ph18040521

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